diff --git a/proxy/metrics.go b/proxy/metrics.go
index 33a517211b3..54e09ad2e92 100644
--- a/proxy/metrics.go
+++ b/proxy/metrics.go
@@ -59,6 +59,23 @@ var (
 			Help:      "Total count of TCP sessions that have been proxied to any origin",
 		},
 	)
+	connectLatency = prometheus.NewHistogram(
+		prometheus.HistogramOpts{
+			Namespace: connection.MetricsNamespace,
+			Subsystem: "proxy",
+			Name:      "connect_latency",
+			Help:      "Time it takes to establish and acknowledge connections in milliseconds",
+			Buckets:   []float64{1, 10, 25, 50, 100, 500, 1000, 5000},
+		},
+	)
+	connectStreamErrors = prometheus.NewCounter(
+		prometheus.CounterOpts{
+			Namespace: connection.MetricsNamespace,
+			Subsystem: "proxy",
+			Name:      "connect_streams_errors",
+			Help:      "Total count of failure to establish and acknowledge connections",
+		},
+	)
 )
 
 func init() {
@@ -69,6 +86,8 @@ func init() {
 		requestErrors,
 		activeTCPSessions,
 		totalTCPSessions,
+		connectLatency,
+		connectStreamErrors,
 	)
 }
 
diff --git a/proxy/proxy.go b/proxy/proxy.go
index 38989a5f0c9..426bca2c110 100644
--- a/proxy/proxy.go
+++ b/proxy/proxy.go
@@ -6,6 +6,7 @@ import (
 	"io"
 	"net/http"
 	"strconv"
+	"time"
 
 	"github.com/pkg/errors"
 	"github.com/rs/zerolog"
@@ -139,7 +140,11 @@ func (p *Proxy) ProxyHTTP(
 			return fmt.Errorf("response writer is not a flusher")
 		}
 		rws := connection.NewHTTPResponseReadWriterAcker(w, flusher, req)
-		if err := p.proxyStream(tr.ToTracedContext(), rws, dest, originProxy); err != nil {
+		connectedLogger := p.log.Debug().
+			Int(management.EventTypeKey, int(management.HTTP)).
+			Str(LogFieldDestAddr, dest).
+			Uint8(LogFieldConnIndex, tr.ConnIndex)
+		if err := p.proxyStream(tr.ToTracedContext(), rws, dest, originProxy, connectedLogger); err != nil {
 			rule, srv := ruleField(p.ingressRules, ruleNum)
 			p.logRequestError(err, cfRay, "", rule, srv)
 			return err
@@ -173,24 +178,22 @@ func (p *Proxy) ProxyTCP(
 
 	tracedCtx := tracing.NewTracedContext(serveCtx, req.CfTraceID, p.log)
 
-	p.log.Debug().
-		Int(management.EventTypeKey, int(management.TCP)).
-		Str(LogFieldFlowID, req.FlowID).
-		Str(LogFieldDestAddr, req.Dest).
-		Uint8(LogFieldConnIndex, req.ConnIndex).
-		Msg("tcp proxy stream started")
+	debugLogger := func() *zerolog.Event {
+		return p.log.Debug().
+			Int(management.EventTypeKey, int(management.TCP)).
+			Str(LogFieldFlowID, req.FlowID).
+			Str(LogFieldDestAddr, req.Dest).
+			Uint8(LogFieldConnIndex, req.ConnIndex)
+	}
+
+	debugLogger().Msg("tcp proxy stream started")
 
-	if err := p.proxyStream(tracedCtx, rwa, req.Dest, p.warpRouting.Proxy); err != nil {
+	if err := p.proxyStream(tracedCtx, rwa, req.Dest, p.warpRouting.Proxy, debugLogger()); err != nil {
 		p.logRequestError(err, req.CFRay, req.FlowID, "", ingress.ServiceWarpRouting)
 		return err
 	}
 
-	p.log.Debug().
-		Int(management.EventTypeKey, int(management.TCP)).
-		Str(LogFieldFlowID, req.FlowID).
-		Str(LogFieldDestAddr, req.Dest).
-		Uint8(LogFieldConnIndex, req.ConnIndex).
-		Msg("tcp proxy stream finished successfully")
+	debugLogger().Msg("tcp proxy stream finished successfully")
 
 	return nil
 }
@@ -294,16 +297,21 @@ func (p *Proxy) proxyHTTPRequest(
 
 // proxyStream proxies type TCP and other underlying types if the connection is defined as a stream oriented
 // ingress rule.
+// connectedLogger is used to log when the connection is acknowledged
 func (p *Proxy) proxyStream(
 	tr *tracing.TracedContext,
 	rwa connection.ReadWriteAcker,
 	dest string,
 	connectionProxy ingress.StreamBasedOriginProxy,
+	connectedLogger *zerolog.Event,
 ) error {
 	ctx := tr.Context
 	_, connectSpan := tr.Tracer().Start(ctx, "stream-connect")
+
+	start := time.Now()
 	originConn, err := connectionProxy.EstablishConnection(ctx, dest)
 	if err != nil {
+		connectStreamErrors.Inc()
 		tracing.EndWithErrorStatus(connectSpan, err)
 		return err
 	}
@@ -313,9 +321,13 @@ func (p *Proxy) proxyStream(
 	encodedSpans := tr.GetSpans()
 
 	if err := rwa.AckConnection(encodedSpans); err != nil {
+		connectStreamErrors.Inc()
 		return err
 	}
 
+	connectLatency.Observe(float64(time.Since(start).Milliseconds()))
+	connectedLogger.Msg("proxy stream established")
+
 	originConn.Stream(ctx, rwa, p.log)
 	return nil
 }